EA010923B1 - Способ сбраживания углеводных субстратов - Google Patents
Способ сбраживания углеводных субстратов Download PDFInfo
- Publication number
- EA010923B1 EA010923B1 EA200600827A EA200600827A EA010923B1 EA 010923 B1 EA010923 B1 EA 010923B1 EA 200600827 A EA200600827 A EA 200600827A EA 200600827 A EA200600827 A EA 200600827A EA 010923 B1 EA010923 B1 EA 010923B1
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- EA
- Eurasian Patent Office
- Prior art keywords
- alcohols
- mixture
- fermentation
- hydrocarbons
- yeast
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
- C12P7/06—Ethanol, i.e. non-beverage
- C12P7/14—Multiple stages of fermentation; Multiple types of microorganisms or re-use of microorganisms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/177—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of a carboxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
- C07C45/505—Asymmetric hydroformylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
- C12P7/06—Ethanol, i.e. non-beverage
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
- C12P7/16—Butanols
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
- C12P7/18—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic polyhydric
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/54—Acetic acid
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51358303P | 2003-10-24 | 2003-10-24 | |
| SE0302800A SE526429C2 (sv) | 2003-10-24 | 2003-10-24 | Metod för att framställa syreinnehållande föreningar utgående från biomassa |
| PCT/SE2004/001534 WO2005040392A1 (en) | 2003-10-24 | 2004-10-22 | Method for producing hydrocarbons and oxygen-containing compounds, from biomass |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200600827A1 EA200600827A1 (ru) | 2006-10-27 |
| EA010923B1 true EA010923B1 (ru) | 2008-12-30 |
Family
ID=34525631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200600827A EA010923B1 (ru) | 2003-10-24 | 2004-10-22 | Способ сбраживания углеводных субстратов |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US20050112739A1 (xx) |
| EP (1) | EP1680509B1 (xx) |
| JP (1) | JP5026082B2 (xx) |
| KR (1) | KR101189818B1 (xx) |
| CN (1) | CN100396779C (xx) |
| AU (1) | AU2004284364B2 (xx) |
| BR (1) | BRPI0415619B1 (xx) |
| CA (1) | CA2541899C (xx) |
| CU (1) | CU23839B1 (xx) |
| CY (1) | CY1122714T1 (xx) |
| DK (1) | DK1680509T3 (xx) |
| EA (1) | EA010923B1 (xx) |
| ES (1) | ES2774700T3 (xx) |
| HK (1) | HK1096428A1 (xx) |
| HR (1) | HRP20200323T1 (xx) |
| HU (1) | HUE048539T2 (xx) |
| IL (1) | IL174793A (xx) |
| LT (1) | LT1680509T (xx) |
| MX (1) | MXPA06004340A (xx) |
| NO (1) | NO341608B1 (xx) |
| PL (1) | PL1680509T3 (xx) |
| PT (1) | PT1680509T (xx) |
| RS (1) | RS20060281A (xx) |
| SE (1) | SE526429C2 (xx) |
| SI (1) | SI1680509T1 (xx) |
| UA (1) | UA84299C2 (xx) |
| WO (1) | WO2005040392A1 (xx) |
| ZA (1) | ZA200602864B (xx) |
Families Citing this family (101)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7074603B2 (en) * | 1999-03-11 | 2006-07-11 | Zeachem, Inc. | Process for producing ethanol from corn dry milling |
| ES2400285T3 (es) * | 1999-03-11 | 2013-04-08 | Zeachem, Inc. | Proceso para producir etanol |
| MX279852B (es) * | 2004-01-29 | 2010-10-08 | Zeachem Inc | Recuperacion de acidos organicos. |
| US7708214B2 (en) | 2005-08-24 | 2010-05-04 | Xyleco, Inc. | Fibrous materials and composites |
| US20150328347A1 (en) | 2005-03-24 | 2015-11-19 | Xyleco, Inc. | Fibrous materials and composites |
| US20070014895A1 (en) * | 2005-07-12 | 2007-01-18 | Holtzapple Mark T | System and Method for Converting Biomass |
| US8273558B2 (en) | 2005-10-26 | 2012-09-25 | Butamax(Tm) Advanced Biofuels Llc | Fermentive production of four carbon alcohols |
| US8129162B2 (en) * | 2007-12-20 | 2012-03-06 | Butamax(Tm) Advanced Biofuels Llc | Ketol-acid reductoisomerase using NADH |
| US8945899B2 (en) * | 2007-12-20 | 2015-02-03 | Butamax Advanced Biofuels Llc | Ketol-acid reductoisomerase using NADH |
| US8450542B2 (en) | 2005-12-16 | 2013-05-28 | Phillips 66 Company | Integrated process for converting carbohydrates to hydrocarbons |
| US7678950B2 (en) | 2005-12-16 | 2010-03-16 | Conocophillips Company | Process for converting carbohydrates to hydrocarbons |
| US20080015397A1 (en) * | 2006-06-16 | 2008-01-17 | D Amore Michael B | Process for making isooctenes from aqueous 1-butanol |
| US20090030239A1 (en) * | 2006-06-16 | 2009-01-29 | D Amore Michael B | Process for making butenes from aqueous isobutanol |
| US20080015396A1 (en) * | 2006-06-16 | 2008-01-17 | D Amore Michael B | Process for making dibutyl ethers from dry isobutanol |
| US20090099401A1 (en) | 2006-06-16 | 2009-04-16 | D Amore Michael B | Process for making isooctenes from aqueous isobutanol |
| US20080015395A1 (en) * | 2006-06-16 | 2008-01-17 | D Amore Michael B | Process for making butenes from aqueous 1-butanol |
| US20080045754A1 (en) * | 2006-06-16 | 2008-02-21 | D Amore Michael B | Process for making butenes from dry 1-butanol |
| US20080132741A1 (en) * | 2006-06-16 | 2008-06-05 | D Amore Michael B | Process for making butenes from dry isobutanol |
| US20080009656A1 (en) * | 2006-06-16 | 2008-01-10 | D Amore Michael B | Process for making isooctenes from dry isobutanol |
| US8975047B2 (en) * | 2006-06-16 | 2015-03-10 | E I Du Pont De Nemours And Company | Process for making isooctenes from dry 1-butanol |
| AP2724A (en) | 2006-07-21 | 2013-08-31 | Xyleco Inc | Conversion systems for biomass |
| JP5013396B2 (ja) * | 2006-09-01 | 2012-08-29 | 独立行政法人産業技術総合研究所 | 炭素数３の多価アルコールの脱水／水素化用触媒及びそれを用いた炭化水素の製造方法 |
| US7915470B2 (en) | 2006-09-08 | 2011-03-29 | Board Of Regents, The University Of Texas System | Coupled electrochemical method for reduction of polyols to hydrocarbons |
| US8521310B2 (en) * | 2006-10-31 | 2013-08-27 | Rockwell Automation Technologies, Inc. | Integrated model predictive control of distillation and dehydration sub-processes in a biofuel production process |
| US8571690B2 (en) * | 2006-10-31 | 2013-10-29 | Rockwell Automation Technologies, Inc. | Nonlinear model predictive control of a biofuel fermentation process |
| US20080103747A1 (en) * | 2006-10-31 | 2008-05-01 | Macharia Maina A | Model predictive control of a stillage sub-process in a biofuel production process |
| US7933849B2 (en) * | 2006-10-31 | 2011-04-26 | Rockwell Automation Technologies, Inc. | Integrated model predictive control of batch and continuous processes in a biofuel production process |
| US7831318B2 (en) * | 2006-10-31 | 2010-11-09 | Rockwell Automation Technologies, Inc. | Model predictive control of fermentation temperature in biofuel production |
| US8634940B2 (en) * | 2006-10-31 | 2014-01-21 | Rockwell Automation Technologies, Inc. | Model predictive control of a fermentation feed in biofuel production |
| JP2010030902A (ja) * | 2006-11-21 | 2010-02-12 | Mitsui Chemicals Inc | エチレンの製造方法 |
| US20080132732A1 (en) * | 2006-12-01 | 2008-06-05 | Leo Ernest Manzer | Process for making butenes from aqueous 2-butanol |
| US20080234523A1 (en) * | 2006-12-01 | 2008-09-25 | Leo Ernest Manzer | Process for making isooctenes from aqueous 2-butanol |
| US20080132730A1 (en) * | 2006-12-01 | 2008-06-05 | Leo Ernest Manzer | Process for making butenes from dry 2-butanol |
| US20080131948A1 (en) * | 2006-12-01 | 2008-06-05 | Leo Ernest Manzer | Process for making isooctenes from dry 2-butanol |
| BRPI0605173A (pt) * | 2006-12-05 | 2008-07-22 | Braskem Sa | processo de produção de uma ou mais olefinas, olefina, e, polìmero |
| MX2009008496A (es) * | 2007-02-09 | 2009-08-20 | Zeachem Inc | Metodos de energia eficiente para producir productos. |
| BRPI0701993A2 (pt) * | 2007-03-30 | 2008-11-18 | Petroleo Brasileiro Sa | mÉtodo para reciclagem e aproveitamento da glicerina obtida da produÇço do biodiesel |
| CN101680007A (zh) | 2007-04-18 | 2010-03-24 | 纳幕尔杜邦公司 | 使用高活性酮醇酸还原异构酶来发酵生产异丁醇 |
| US8153850B2 (en) * | 2007-05-11 | 2012-04-10 | The Texas A&M University System | Integrated biofuel production system |
| WO2009003039A1 (en) * | 2007-06-25 | 2008-12-31 | Mcneff Research Consultants, Inc. | Catalysts, systems and methods for ether synthesis |
| BRPI0812596A2 (pt) * | 2007-06-27 | 2014-12-30 | Novozymes As | Método para a produção de um produto de fermentação a partir de um material contendo lignocelulose |
| EP2017346A1 (en) * | 2007-07-19 | 2009-01-21 | Ineos Europe Limited | Process for the production of alcohols |
| PL3135747T3 (pl) | 2007-07-20 | 2021-07-19 | Upm-Kymmene Oyj | Sposób i urządzenie do wytwarzania ciekłego produktu węglowodorowego ze stałej biomasy |
| US9145566B2 (en) * | 2007-07-27 | 2015-09-29 | Swift Fuels, Llc | Renewable engine fuel and method of producing same |
| UA98002C2 (uk) * | 2007-09-07 | 2012-04-10 | Фураникс Технолоджиз Б.В. | Спосіб одержання суміші похідних фурфуралю і 5-алкоксиметилфурфуралю та паливо, що містить таку суміш |
| US8193402B2 (en) * | 2007-12-03 | 2012-06-05 | Gevo, Inc. | Renewable compositions |
| KR20100095004A (ko) * | 2007-12-03 | 2010-08-27 | 게보 인코포레이티드 | 재생 조성물 |
| BRPI0815408B1 (pt) * | 2007-12-05 | 2021-08-24 | Braskem S.A. | Processo integrado para a produção de copolímeros de etileno e butileno, copolímero de etileno e butileno, e, uso de etileno e 1-butileno |
| MX2010007210A (es) * | 2007-12-27 | 2010-10-08 | Gevo Inc | Recuperacion de alcoholes superiores a partir de soluciones acuosas diluidas. |
| WO2009091783A2 (en) * | 2008-01-14 | 2009-07-23 | Pennsylvania Sustainable Technologies, Llc | Method and system for producing alternative liquid fuels or chemicals |
| US7932297B2 (en) | 2008-01-14 | 2011-04-26 | Pennsylvania Sustainable Technologies, Llc | Method and system for producing alternative liquid fuels or chemicals |
| AU2009212131A1 (en) * | 2008-02-07 | 2009-08-13 | Zeachem Inc. | Indirect production of butanol and hexanol |
| KR100970936B1 (ko) * | 2008-04-25 | 2010-07-20 | 한국에너지기술연구원 | 가스화장치를 이용한 바이오디젤 정제 잔여물의 가스화방법 |
| EP2274435A4 (en) * | 2008-05-07 | 2012-06-20 | Zeachem Inc | RECOVERING ORGANIC ACIDS |
| FR2931477B1 (fr) * | 2008-05-21 | 2012-08-17 | Arkema France | Acide cyanhydrique derive de matiere premiere renouvable |
| FR2934264B1 (fr) * | 2008-07-22 | 2012-07-20 | Arkema France | Fabrication d'esters de vinyle a partir de matieres renouvelables, esters de vinyle obtenus et utilisations |
| FR2934261B1 (fr) * | 2008-07-25 | 2015-04-10 | Arkema France | Procede de synthese d'esters de l'acide acrylique |
| FR2938535B1 (fr) * | 2008-11-20 | 2012-08-17 | Arkema France | Procede de fabrication de methylmercaptopropionaldehyde et de methionine a partir de matieres renouvelables |
| FR2938838B1 (fr) * | 2008-11-27 | 2012-06-08 | Arkema France | Procede de fabrication d'un methacrylate de methyle derive de la biomasse |
| WO2010075437A2 (en) * | 2008-12-22 | 2010-07-01 | Sartec Corporation | Systems and methods for producing fuels and fuel precursors from carbohydrates |
| FR2940801B1 (fr) * | 2009-01-06 | 2012-08-17 | Arkema France | Procede de fabrication d'un methacrylate de methyle derive de la biomasse |
| KR20170076823A (ko) | 2009-01-26 | 2017-07-04 | 질레코 인코포레이티드 | 바이오매스의 가공처리방법 |
| BRPI1008287A2 (pt) * | 2009-02-24 | 2016-03-15 | Gevo Inc | métodos de preparação de butadieno e isopreno renováveis |
| LT2403894T (lt) * | 2009-03-03 | 2016-09-26 | The Coca-Cola Company | Biologinės kilmės polietileno tereftalamo pakuotė ir jos gamybos būdas |
| FR2945543B1 (fr) * | 2009-05-15 | 2011-05-06 | Inst Francais Du Petrole | Procede de production d'alcools et/ou de solvants a partir de biomasse lignocellulosique avec recyclage acide des residus solides |
| US8802905B2 (en) | 2009-06-19 | 2014-08-12 | The Texas A&M University System | Integrated biofuel processing system |
| MX2012007583A (es) | 2009-12-29 | 2012-07-30 | Butamax Tm Advanced Biofuels | Alcohol deshidrogenasas (adh) utiles para la produccion fermentativa de alcoholes alquilicos de cadena corta. |
| KR101664450B1 (ko) * | 2010-01-08 | 2016-10-11 | 한국과학기술원 | 바이오매스로부터 유기산을 생산하는 방법 |
| WO2011085223A1 (en) | 2010-01-08 | 2011-07-14 | Gevo, Inc. | Integrated methods of preparing renewable chemicals |
| US20110287497A1 (en) * | 2010-04-26 | 2011-11-24 | Holtzapple Mark T | Anaerobic organisms in a process for converting biomass |
| EP2566830B1 (en) | 2010-05-07 | 2017-03-22 | GEVO, Inc. | Renewable jet fuel blendstock from isobutanol |
| KR101089488B1 (ko) | 2010-07-14 | 2011-12-02 | 주식회사 엘지화학 | 올레핀으로부터 이소타입의 알데히드와 알콜의 병산 장치 및 이를 이용한 병산 방법 |
| JP6099623B2 (ja) | 2011-03-24 | 2017-03-22 | ビュータマックス・アドバンスド・バイオフューエルズ・エルエルシー | イソブタノール生成のための宿主細胞及び方法 |
| TW201247596A (en) | 2011-04-19 | 2012-12-01 | Gevo Inc | Variations on prins-like chemistry to produce 2,5-dimethylhexadiene from isobutanol |
| FR2976293B1 (fr) * | 2011-06-10 | 2015-01-02 | Arkema France | Procede de synthese de composes hydrocarbones bi-fonctionnels a partir de biomasse |
| US8871051B2 (en) | 2012-03-21 | 2014-10-28 | Los Alamos National Security, Llc | Process for decomposing lignin in biomass |
| KR20150014953A (ko) | 2012-05-11 | 2015-02-09 | 부타맥스 어드밴스드 바이오퓨얼스 엘엘씨 | 케톨-산 리덕토아이소머라아제 효소 및 사용 방법 |
| WO2014047421A1 (en) | 2012-09-21 | 2014-03-27 | Butamax(Tm) Advanced Biofuels Llc | Production of renewable hydrocarbon compositions |
| CN105102616A (zh) | 2012-09-26 | 2015-11-25 | 布特马斯先进生物燃料有限责任公司 | 具有酮醇酸还原异构酶活性的多肽 |
| US9914672B2 (en) | 2012-10-19 | 2018-03-13 | Lummus Technology Inc. | Conversion of alcohols to distillate fuels |
| FR2997397B1 (fr) * | 2012-10-29 | 2014-11-07 | Arkema France | Procede de synthese directe d'aldehydes insatures a partir de melanges d'alcools |
| KR101450089B1 (ko) | 2012-12-20 | 2014-10-15 | 한국과학기술연구원 | 산-금속 복합촉매를 이용하여 벤질페닐에테르를 포함하는 바이오매스로부터 고탄소의 포화탄화수소를 생산하는 방법 |
| US8889386B2 (en) | 2013-04-11 | 2014-11-18 | Hankyong Industry Academic Cooperation Center | Method for producing bio-alcohol using nanoparticles |
| BR102013022434B8 (pt) * | 2013-09-02 | 2022-06-21 | Advel Tecnologia E Comercio Eireli | Processo para fermentação microbiana de substratos açucarados |
| FR3019545B1 (fr) * | 2014-04-04 | 2016-03-11 | Arkema France | Procede de synthese directe de (meth)acroleine a partir d'ethers et/ou acetals |
| WO2015174518A1 (ja) * | 2014-05-15 | 2015-11-19 | 株式会社Ｉｈｉ環境エンジニアリング | バイオマスを用いた液体燃料製造方法 |
| WO2015174520A1 (ja) * | 2014-05-15 | 2015-11-19 | 株式会社Ｉｈｉ環境エンジニアリング | 植物加工システム |
| DE102015002830B4 (de) | 2015-03-05 | 2019-05-23 | Hochschule Furtwangen | Bioraffinerie-Verfahren |
| WO2016194727A1 (ja) * | 2015-05-29 | 2016-12-08 | 横浜ゴム株式会社 | 老化防止剤の製造方法 |
| AU2016282708A1 (en) * | 2015-06-23 | 2018-02-08 | Minn-Dak Farmers Cooperative | Process for saponin enhanced autoloysis of yeast |
| US10239812B2 (en) | 2017-04-27 | 2019-03-26 | Sartec Corporation | Systems and methods for synthesis of phenolics and ketones |
| WO2019027997A1 (en) * | 2017-07-31 | 2019-02-07 | Synata Bio, Inc. | SYSTEM AND METHOD FOR CONCENTRATING SUSPENDED SOLID MATERIALS BEFORE REMOVAL |
| CN108244628A (zh) * | 2018-01-18 | 2018-07-06 | 路传章 | 一种富含多肽-金属螯合物的营养液及其制备方法和应用 |
| US10696923B2 (en) | 2018-02-07 | 2020-06-30 | Sartec Corporation | Methods and apparatus for producing alkyl esters from lipid feed stocks, alcohol feedstocks, and acids |
| US10544381B2 (en) | 2018-02-07 | 2020-01-28 | Sartec Corporation | Methods and apparatus for producing alkyl esters from a reaction mixture containing acidified soap stock, alcohol feedstock, and acid |
| US11512035B2 (en) | 2018-09-17 | 2022-11-29 | Exxonmobil Chemical Patents Inc. | Transfer hydroformylation for the production of oxygenates |
| KR102272012B1 (ko) * | 2019-11-06 | 2021-07-01 | 세종대학교산학협력단 | 혐기성소화조의 중간생성물을 이용한 바이오알코올의 제조방법 |
| JP7535378B2 (ja) * | 2020-01-20 | 2024-08-16 | 出光興産株式会社 | アルデヒド化合物の製造方法及び炭化水素化合物の製造方法 |
| IL311105A (en) * | 2021-08-31 | 2024-04-01 | Swedish Biofuels Ab | A method for producing motor fuel from ethanol |
| DK4141090T3 (da) * | 2021-08-31 | 2023-11-20 | Swedish Biofuels Ab | Fremgangsmåde til fremstilling af motorbrændstof fra ethanol |
| IT202200004013A1 (it) * | 2022-03-03 | 2023-09-03 | Milano Politecnico | Processo autosostenibile a zero emissioni per produzione di chemicals da fonti organiche |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4326032A (en) * | 1979-08-20 | 1982-04-20 | Grove Leslie H | Process for the production of organic fuel |
| US5173429A (en) * | 1990-11-09 | 1992-12-22 | The Board Of Trustees Of The University Of Arkansas | Clostridiumm ljungdahlii, an anaerobic ethanol and acetate producing microorganism |
| US6509180B1 (en) * | 1999-03-11 | 2003-01-21 | Zeachem Inc. | Process for producing ethanol |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1725084A (en) * | 1927-11-08 | 1929-08-20 | Eastern Alcohol Corp | Process of producing fusel oil by fermentation |
| US2272982A (en) * | 1938-07-19 | 1942-02-10 | Owen William Ludwell | Process for increasing fermentative efficiency in ethanol production |
| US4066793A (en) * | 1974-03-18 | 1978-01-03 | Ajinomoto Co., Inc. | Seasoning composition and preparation thereof |
| US4342831A (en) * | 1979-07-02 | 1982-08-03 | American Can Company | Fermentable acid hydrolyzates and fermentation process |
| DE3303571C2 (de) * | 1982-03-11 | 1984-07-26 | Buckau-Walther AG, 4048 Grevenbroich | Verfahren und Anlage zur Herstellung von Äthanol |
| US4571384A (en) * | 1982-10-18 | 1986-02-18 | State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Oregon State University | Methane production |
| ZA838867B (en) * | 1982-12-01 | 1984-07-25 | Thomas Anthony Carson | Fermentation method and composition for use therein |
| JPS6317696A (ja) * | 1986-07-08 | 1988-01-25 | Shinenerugii Sogo Kaihatsu Kiko | アルコ−ルの発酵方法 |
| US5070016A (en) * | 1991-03-28 | 1991-12-03 | Revolution Fuels Of America, Inc. | Integrated process for producing ethanol, methanol and butyl ethers |
| US6265619B1 (en) * | 1996-01-17 | 2001-07-24 | Exxon Chemical Patents Inc. | Oxygenates and processes for their manufacture |
| US6130076A (en) * | 1997-06-19 | 2000-10-10 | University Of Florida Research Foundation, Inc. | Ethanol production using a soy hydrolysate-based medium or a yeast autolysate-based medium |
| FI106955B (fi) * | 1998-10-16 | 2001-05-15 | Fortum Oil & Gas Oy | Menetelmä iso-oktaanin valmistamiseksi isobuteenipitoisesta hiilivetysyötöstä |
| RU2145354C1 (ru) | 1998-11-24 | 2000-02-10 | Оренбургский государственный университет | Способ подготовки зернового крахмалсодержащего сырья для спиртового брожения |
| US6740508B2 (en) * | 1999-02-11 | 2004-05-25 | Renessen Llc | Fermentation-based products from corn and method |
| WO2001018154A1 (en) * | 1999-09-06 | 2001-03-15 | Agrofuel Ab | Motor fuel for diesel engines |
| JP2002345395A (ja) * | 2001-05-30 | 2002-12-03 | Kumiko Ibaraki | シュー生地用配合組成物 |
-
2003
- 2003-10-24 SE SE0302800A patent/SE526429C2/sv not_active IP Right Cessation
-
2004
- 2004-10-22 SI SI200432486T patent/SI1680509T1/sl unknown
- 2004-10-22 CN CNB2004800313034A patent/CN100396779C/zh not_active Expired - Lifetime
- 2004-10-22 WO PCT/SE2004/001534 patent/WO2005040392A1/en active Application Filing
- 2004-10-22 HU HUE04793835A patent/HUE048539T2/hu unknown
- 2004-10-22 MX MXPA06004340A patent/MXPA06004340A/es active IP Right Grant
- 2004-10-22 US US10/970,835 patent/US20050112739A1/en not_active Abandoned
- 2004-10-22 AU AU2004284364A patent/AU2004284364B2/en not_active Expired
- 2004-10-22 RS YUP-2006/0281A patent/RS20060281A/sr unknown
- 2004-10-22 CA CA2541899A patent/CA2541899C/en not_active Expired - Lifetime
- 2004-10-22 UA UAA200604052A patent/UA84299C2/ru unknown
- 2004-10-22 EP EP04793835.2A patent/EP1680509B1/en not_active Expired - Lifetime
- 2004-10-22 PL PL04793835T patent/PL1680509T3/pl unknown
- 2004-10-22 KR KR1020067007926A patent/KR101189818B1/ko active IP Right Grant
- 2004-10-22 EA EA200600827A patent/EA010923B1/ru not_active IP Right Cessation
- 2004-10-22 LT LTEP04793835.2T patent/LT1680509T/lt unknown
- 2004-10-22 DK DK04793835.2T patent/DK1680509T3/da active
- 2004-10-22 JP JP2006536486A patent/JP5026082B2/ja not_active Expired - Lifetime
- 2004-10-22 PT PT47938352T patent/PT1680509T/pt unknown
- 2004-10-22 ES ES04793835T patent/ES2774700T3/es not_active Expired - Lifetime
- 2004-10-22 BR BRPI0415619-6B1A patent/BRPI0415619B1/pt active IP Right Grant
-
2006
- 2006-04-04 IL IL174793A patent/IL174793A/en active IP Right Grant
- 2006-04-07 ZA ZA200602864A patent/ZA200602864B/en unknown
- 2006-04-24 CU CU2006000087A patent/CU23839B1/es not_active IP Right Cessation
- 2006-05-23 NO NO20062346A patent/NO341608B1/no unknown
-
2007
- 2007-03-30 HK HK07103434.1A patent/HK1096428A1/xx not_active IP Right Cessation
-
2014
- 2014-11-06 US US14/534,490 patent/US20150064763A1/en not_active Abandoned
-
2020
- 2020-02-25 HR HRP20200323TT patent/HRP20200323T1/hr unknown
- 2020-02-28 CY CY20201100186T patent/CY1122714T1/el unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4326032A (en) * | 1979-08-20 | 1982-04-20 | Grove Leslie H | Process for the production of organic fuel |
| US5173429A (en) * | 1990-11-09 | 1992-12-22 | The Board Of Trustees Of The University Of Arkansas | Clostridiumm ljungdahlii, an anaerobic ethanol and acetate producing microorganism |
| US6509180B1 (en) * | 1999-03-11 | 2003-01-21 | Zeachem Inc. | Process for producing ethanol |
Non-Patent Citations (1)
| Title |
|---|
| STN International, File CAPLUS, CAPLUS accession no. 1988:189891, Document no. 108:189891, Shin Energy Sogo Kaihatsu Kiko: "Manufacture of ethanol with Zymomonas cultured in media containing specific amino acids"; & JP.A2,63017696, 19880125 * |
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